1,2-Dichloroethane → HCID 178513586, compound

HRID 1297193Notes

Reaction equation

HRID 1297193 reaction equation
[C:1](O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([C:38]([NH2:40])=[O:39])=[CH:37][C:31]=3[N:30]=2)=[CH:25][CH:24]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([C:38]([NH2:40])=[O:39])=[CH:37][C:31]=3[N:30]=2)=[CH:27][CH:28]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 178513585HCID 178513585, compound

Product 1

HCID 178513586HCID 178513586, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of benzoic acid (75 mg, 0.62 mmol) and EDC (59 mg, 0.31 mmol) in DMF (1 mL) was stirred for 2 h and then was treated with 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (75 mg, 0.21 mmol) and DMAP (65 mg, 0.53 mmol). The mixture was stirred for 18 h, and the crude material was purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA), providing 46 mg (66%) of the title compound. HPLC (Method C): Rt=5.15. MS (ESI+): mass calcd. for C28H28N4O3, 468.22; m/z found, 469.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.19 (s, 1H), 8.00-7.96 (m, 3H), 7.72 (d, J=8.6 Hz, 1H), 7.36-7.25 (m, 2H), 7.25-7.10 (m, 4H), 6.95-6.90 (m, 1H), 4.20-4.07 (m, 2H), 3.92-3.90 (m, 1H), 3.48-3.43 (m, 1H), 2.45-2.35 (m, 1H), 2.12-1.81 (m, 1H), 1.81-1.30 (m, 7H).

Workup

  1. customthe crude material was purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA)

Sources & evidence

ORD record
ord-1e27ff44c4704aa2af1de0b64b571172
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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